The context to enhance proactive service performance needs to be investigated in the hotel industry because extra service efforts are needed to fulfill customer needs. This study aims to investigate the contextual impact of paradoxical leadership(PL) on proactive service performance(PS) mediated through trust in leader(TL). Paradoxical leadership includes five kinds of integration including uniformity and individualization(UI), self-centeredness and other-centeredness(SO), decision control and autonomy(CA), work requirements and flexibility(RF), and distance and closeness(DC). Focused on the hotel industry, the relationships among PL, TL, and PS have been hypothesized based on the existing literature. This study surveys the front-of-house employees of five star hotels using convenience sampling. The number of 272 cases was used for actual analysis and the results were explained using structural equation modeling. The results firstly indicate that CA made a significantly positive influence on TL whereas the impacts of UI, SO, RF, and DC were rejected Secondly UI, CA, and RF positively influenced PS whereas the impacts of SO and DC were rejected. Thirdly TL makes a significant impact on PS. Finally TL mediates for the relationship between CA and PS. This study indicates the context to enhance PS and discusses how to develop paradoxical leadership.